No min. stay. Travel through early May. Fare can be bought one-way for half the lowest roundtrip price. No peak holiday travel at this price.

Travel valid December 27, 2016, through May 8, 2017.

This is a fare from Southwest, please visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.

To the best of our knowledge, there is a reasonable amount of seat availability at the stated price. Flexible travel dates may be required to find this rate; seats may not be available on all flights or all dates of travel. Holiday periods may be excluded. We monitor the availability of the fare and take efforts to remove and/or modify fares when no longer available.

All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included. Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

No min. stay. Travel through early May. Fare can be bought one-way for half the lowest roundtrip price. No peak holiday travel at this price.

Travel valid December 27, 2016, through May 8, 2017.

This is a fare from Southwest, please visit Southwest.com to find this fare. Other airlines often match Southwest sales, so search other sites to find the best option.

To the best of our knowledge, there is a reasonable amount of seat availability at the stated price. Flexible travel dates may be required to find this rate; seats may not be available on all flights or all dates of travel. Holiday periods may be excluded. We monitor the availability of the fare and take efforts to remove and/or modify fares when no longer available.

All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included. Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

I really like the numbered positions for boarding now. It seems alot easier and fair in their boarding process. It helps the passinger's not having to stand in line to get a good position and since we are in our 70's it is very important not to have to stand a long time. It was also very fast.

"comfortable seats, on time , good value"

reviewed by an Airfarewatchdog Traveler on August 17, 2010

Flight from Cleveland to Chicago

Airline: Southwest

RT/OW: roundtrip

Date of Flight: August 2010

Seat Class: economy

Check-in Experience

In-flight Service

Seat Comfort

It was a bit bumpy but the seats were comfortable if not too wide the open seating was interesting I got to sit with my friends both ways but sat far back than usual. Boarding was quick and orderly same for deplaning
I would fly them again this was my first experience. My suitcase was mashed both ways broke the mirror in my cosmetic bag lid and broke the ridged in side corner of my soft luggage. Every seat full both ways.

Found by other travelers:Cleveland, OH(CLE)toChicago, IL(MDW)

$714

Flight from Cleveland to Chicago (CLE - MDW)

Wed, Jun 11 - Thu, Jun 19

Delta

$336

Flight from Cleveland to Chicago (CLE - MDW)

Sun, Jul 27 - Thu, Jul 31

Delta

$212

Flight from Cleveland to Chicago (CLE - MDW)

Wed, Aug 27 - Sun, Aug 31

Delta

$660

Flight from Cleveland to Chicago (CLE - MDW)

Mon, Jun 16 - Mon, Jun 16

Delta

$648

Flight from Cleveland to Chicago (CLE - MDW)

Sun, Jun 22 - Tue, Jun 24

Delta

$516

Flight from Cleveland to Chicago (CLE - MDW)

Fri, Jun 20 - Mon, Jun 23

Delta

$294

Flight from Cleveland to Chicago (CLE - MDW)

Sat, Oct 25 - Sun, Nov 2

Delta

$630

Flight from Cleveland to Chicago (CLE - MDW)

Wed, Jun 11 - Fri, Jun 13

Delta

$265

Flight from Cleveland to Chicago (CLE - MDW)

Thu, Jul 10 - Tue, Jul 15

Delta

$290

Flight from Cleveland to Chicago (CLE - MDW)

Thu, Jul 3 - Sun, Jul 6

Delta

There are approximately 12 flights covering the route from Hopkins International Airport in Cleveland to Midway Airport in Chicago, provided by as many as 2 airlines.

The following airlines often offer cheap flights from Cleveland to Chicago